IPod Classic 80-gig won't transfer purchases to iTunes Library, nor will it sync. Please help!

     My iPod Classic 80gb will not transfer purchases to my iTunes library. When I click the "Transfer Purchase" button, it says it's working, but then I get a pop-up which reads 'Attempting to copy the disk "OS" failed. An unknown error occurred (-69)', and following that pop-up is another pop-up, which reads 'The iPod "William's iPod" cannot be synced. An unknown error occurred (-69).
     I need to transfer the purchases, because I had to restore my laptop (Which is a PC, by the way) to the original factory settings, and I had to re-download iTunes. When I re-downloaded it, I logged in and everything, but all my music was missing. I clicked the "Purchase History" button in the account part, and I clicked the "Download" button in order to regain my lost music, and I waited about 45 minutes or so, only to come back to iTunes saying it had finished, when it had only re-downloaded 75 of my 279 songs.
     After this, I went into the help section of iTunes. In that, I clicked "Manage your media files," and from there, I clicked on "Find iTunes files." So, I did what it told me to do, which was to run a full scan on my PC, and I looked everywhere I could think of, and everywhere iTunes suggested my missing music might be located, only to find that I wasted my time.
     I am a musician, I CRAVE the music I listen to, and I'm constantly finding new stuff to listen to and research, and if I can't transfer my purchases or sync my device to my library, then that means I can't get new music to listen to on the go, and for me, that is an extreme issue. Obviously, restoring my device is not  an option, because I have nothing to sync it to to get my music back.
     Please, if anyone can help me with my situation, I'd be forever grateful.
*Extra Information*
Laptop- PC, Dell XPS15, has Windows 7, has an intel Core i5 processor, only about 2 and a half months old.
iPod- iPod Classic, 80-gigabytes, I've had it for, going on 5 and 1/4 years now, give or take a few months.

An app called CopyTrans may help get tunes from your iPod to your computer.

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